Search Country Houses in Chatham

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Check prices for these dates

Next weekend
Dec 19 - Dec 21
In two weeks
Dec 26 - Dec 28
In one month
Jan 9 - Jan 11
In two months
Feb 6 - Feb 8
No exact matches found, but these alternatives could be just right

Recommended hotels in Chatham

Dining
Sugar Shack - 300 square feet of pure sweetness.

Sugar Shack - 300 square feet of pure sweetness.

Sugar Shack - 300 square feet of pure sweetness.
2.0 star property
Chatham
10.0 out of 10, Exceptional, (3)
"By far one of my favorite rentals. Everything was perfect and the details were amazing. Not only do I highly recommend, I amSURE I will be returning soon. "
United States
Sue G.
$332 nightly
The price is $374
Dec 16 - Dec 17
Total with taxes and fees
Sugar Shack - 300 square feet of pure sweetness.
Terrace/patio
BLUSH: Boutique TINY home*private spa*walk to town

BLUSH: Boutique TINY home*private spa*walk to town

BLUSH: Boutique TINY home*private spa*walk to town
Chatham
10.0 out of 10, Exceptional, (6)
"We loved this property. All the bells and whistles as far as amenities go for a Vrbo! Great location and place to unwind, unplug ,and reconnect!"
United States
scott B.
$303 nightly
The price is $342
Dec 16 - Dec 17
Total with taxes and fees
BLUSH: Boutique TINY home*private spa*walk to town
Fridge, microwave, oven, stovetop
HunnyHAUS: Deluxe TINY*private spa*walk to town

HunnyHAUS: Deluxe TINY*private spa*walk to town

HunnyHAUS: Deluxe TINY*private spa*walk to town
Chatham
10.0 out of 10, Exceptional, (9)
"Huny House was the most artistically created space we stayed in on our entire trip! We were sooo impressed and appreciated the attention to detail!"
Canada
Patti S.
$360 nightly
The price is $406
Dec 14 - Dec 15
Total with taxes and fees
HunnyHAUS: Deluxe TINY*private spa*walk to town
Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed) | In-room safe, individually decorated, individually furnished, desk
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
Pittsfield
8.6 out of 10, Excellent, (1000)
"I have stayed here many times and it is consistently a comfortable, clean and quiet place."
United States
Jeanine
$94 nightly
The price is $105
Jan 4 - Jan 5, 2026
Total with taxes and fees
Best Western Plus Berkshire Hills Inn & Suites
Exterior
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1002)
"Friendly staff, very clean room and super comfy bed"
United States
Linda
$75 nightly
The price is $84
Dec 24 - Dec 25
Total with taxes and fees
The Yankee, Trademark Collection by Wyndham
Lobby
Element Lenox Berkshires

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.8 out of 10, Exceptional, (11)
"New hotel very nice"
United States
joel
$131 nightly
The price is $146
Dec 21 - Dec 22
Total with taxes and fees
Element Lenox Berkshires
Mini-fridge, stovetop, cookware/dishes/utensils, paper towels
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
2.0 star property
Catskill
9.6 out of 10, Exceptional, (107)
"The hospitality and making sure our stay was enjoyable most of all our needs during the time being. "
United States
Yessica
$159 nightly
The price is $172
Dec 14 - Dec 15
Total with taxes and fees
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
Garden
Shaker Mill Inn

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (437)
"Nice place, easy check in"
United States
Robert
$102 nightly
The price is $112
Dec 14 - Dec 15
Total with taxes and fees
Shaker Mill Inn
Exterior
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
Great Barrington
8.8 out of 10, Excellent, (707)
"Great hospitality "
United States
regina maria
$107 nightly
The price is $120
Dec 17 - Dec 18
Total with taxes and fees
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Lobby
Quality Inn Great Barrington

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.4 out of 10, Very Good, (1002)
"Clean room, nice location "
United States
Devron
$76 nightly
The price is $85
Dec 28 - Dec 29
Total with taxes and fees
Quality Inn Great Barrington
Desk, iron/ironing board, free WiFi, bed sheets
Berkshire Inn

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (840)
"This hotel was very quiet and clean in an excellent spot , and all amenities were very comfortable and convenient I would definitely stay here again."
United States
MARIA J
$79 nightly
The price is $89
Dec 14 - Dec 15
Total with taxes and fees
Berkshire Inn
Desk, laptop workspace, blackout drapes, iron/ironing board
Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
West Stockbridge
6.8 out of 10, (1002)
"Priced very reasonably and the room was clean and comfy!"
United States
Wayne
$51 nightly
The price is $56
Jan 8 - Jan 9, 2026
Total with taxes and fees
Pleasant Valley Motel West Stockbridge
Exterior
the Alander

the Alander

the Alander
2.5 star property
Copake
9.0 out of 10, Wonderful, (188)
"The Alander has such a fun story, and was a great stay. We were just passing through for the night and it had everything we could need! It reminded me of Rosebud Motel group from Schitts Creek ;) if you know you know! Will definitely be staying again!"
United States
Jenna
$140 nightly
The price is $157
Dec 14 - Dec 15
Total with taxes and fees
the Alander
Restaurant
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
8.0 out of 10, Very Good, (986)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
$93 nightly
The price is $104
Dec 16 - Dec 17
Total with taxes and fees
Holiday Inn & Suites Pittsfield-Berkshires by IHG
In-room safe, blackout drapes, iron/ironing board, free WiFi
Pocketbook Hotel and Bath

Pocketbook Hotel and Bath

Pocketbook Hotel and Bath
2.0 star property
Hudson
8.4 out of 10, Very Good, (10)
"lovely place!"
United States
Samyuktha
$262 nightly
The price is $297
Dec 17 - Dec 18
Total with taxes and fees
Pocketbook Hotel and Bath
Room, 2 Queen Beds, Non Smoking | Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi
Monument Mountain Motel

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (805)
"Yes it was clean & staff was very polite. "
United States
Barbara L.
$67 nightly
The price is $74
Dec 14 - Dec 15
Total with taxes and fees
Monument Mountain Motel
Miscellaneous
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.0 out of 10, Wonderful, (1000)
"The staff was so kind and helpful and the rooms were clean and comfortable. This is now my go-to place to stay in the Berkshires!"
United States
Elisabeth
$101 nightly
The price is $113
Dec 23 - Dec 24
Total with taxes and fees
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Porch
Lakehouse Inn

Lakehouse Inn

Lakehouse Inn
4.0 star property
Lee
9.6 out of 10, Exceptional, (290)
"A charming inn in the center of the Berkshires."
United States
Danny
$191 nightly
The price is $213
Dec 19 - Dec 20
Total with taxes and fees
Lakehouse Inn
Suite, Multiple Beds (2 Queen Beds with Sofa bed) | Pillowtop beds, in-room safe, desk, iron/ironing board
Holiday Inn Express Hotel & Suites West Coxsackie by IHG

Holiday Inn Express Hotel & Suites West Coxsackie by IHG

Holiday Inn Express Hotel & Suites West Coxsackie by IHG
2.5 star property
West Coxsackie
8.4 out of 10, Very Good, (980)
"Perfect spot for an overnight stay when coming to the area"
United States
Lisa
$83 nightly
The price is $90
Jan 4 - Jan 5, 2026
Total with taxes and fees
Holiday Inn Express Hotel & Suites West Coxsackie by IHG
Lobby
Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very Good, (1002)
"Room was clean and comfortable; location was good with a breakfast restaurant next door. The in-house breakfast was OK, but we preferred an upgrade. Receptionist staff member was professional and pleasant. "
United States
Patrick
$89 nightly
The price is $99
Dec 28 - Dec 29
Total with taxes and fees
Quality Inn Lee - Lenox South
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chatham Hotel Reviews

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"My husband and I needed a night away between the holidaze and it was perfect! Cozy, clean and warm fireplace to nurture us during a cold snap! Shelly went above and beyond to ensure that we were comfortable and in the quietest part of the hotel. We are booking our family members there"
Sara 1-night trip
Posted 2 days ago
The Yankee, Trademark Collection by Wyndham

Find out more about Chatham

Chatham Country Houses information

Number of reviews
11,340
Accommodation
1 Country Houses
Lowest Price
$56
Highest Price
$406